I know that it's not politically correct to single out groups based on their minority status. It's barbaric, repressive, and generally not very nice. That having been said, I have one question: what if you're singling them out to say something nice?
This isn't an idle question. You see, I really enjoy vacationing in "gay" areas. Yes, this is a major generalization. Here are a few more: based on my exploration of San Francisco's Castro district, Provincetown, Fire Island, and Dupont Circle, I'd have to say that, generally speaking, gay-friendly spots tend to be beautiful and clean, have great food, offer an outstanding music and arts scene, and are often reasonably priced.
Now that I'm out of the rainbow tourism closet, I'll go a little further. Of all the "gay" spots that I've visited, my favorite is Provincetown, Massachusetts. Situated at the very end of Cape Cod, the directions to Provincetown are exceedingly simple: get on Route 6 and drive until there isn't any more road.
If you wish, you can also fly in or take the ferry from Boston. For my money, though, driving is the way to go; it's a fun road trip that takes you through Truro, Wellfleet, and all the other great outer-cape towns. You also go past a couple of great lighthouses, including the Cape Cod Light (which allows tours) and the Chatham Light (which doesn't). If you wish, you can stop off at the Marconi Area, where Guglielmo Marconi built a radio station that carried the world's first transatlantic radio transmission. Alternately, you can see First Encounter Beach, where the Pilgrims first met the Indians.
Once you get to town, find a place to spend the night: although you certainly can take a day trip to P-town, doing so will leave you rushed and unsatisfied. Besides, lodging choices are plentiful and relatively inexpensive: in addition to the ubiquitous Holiday Inn that lurks just outside of town, Provincetown is loaded with guest houses, small hotels, bed and breakfasts, and private room rentals. My personal favorite guest house is the Elephant Walk, which has a comfortable quasi-Victorian atmosphere, friendly owners, and very reasonable rates.
Having set up your accommodations, go exploring! Provincetown is rich in history and culture, and it's hard to be bored there. Although best known for its more recent residents, including John Reed, Eugene O'Neill, John Waters, Anais Nin, Tennessee Williams, Jackson Pollack, and Willem DeKooning, Provincetown once played host to the Pilgrims, who signed the Mayflower Compact in its harbor. Although the Pilgrims soon left, their brief visit is commemorated with the Pilgrim Monument, a 252-foot tall tower that you can climb up, if your feet are willing. Afterwards, you might want to wander around the Provincetown museum, which covers the town's history from seafaring days to the present.
Because of its locale, Provincetown has always attracted ocean-going folk, including the Portuguese, who left a major cultural imprint on the area. To this day, Portuguese snacks are easy to find in town: stands on the main pier sell inexpensive delights like Linguica rolls and kale soup, and the Portuguese Bakery offers great prices on traditional breads and pastries.
If Portuguese food isn't your thing, you might visit a pizzeria (I really like Spiritus), or go to one of the many small, informal restaurants. One of the best is Bubala's, which has delicious, reasonably-priced sandwiches. On the other hand, if you're in the mood for a splurge, you might try one of the pricier seafood restaurants or bistros. Or, if you just want something sweet, drop in at Cabot's Candies or the Provincetown Fudge Factory.
While you're wandering up and down Commercial Street, be sure to check out the endless galleries, bookstores, witchcraft shops, perfumers, antique shops, and little boutiques. In particular, you shouldn't miss Shop Therapy, one of the coolest stores in existence, and Marine Specialties, the absolutely unbelievable surplus store on Commercial Street (this isn't an exaggeration. This place is incredibly awesome).
After a day of wandering, if you still have the stamina, check out Provincetown's nighlife. The town is bursting with things to do after dark, ranging from relaxed neighborhood bars, to raucous clubs, to some truly outstanding drag shows. If your tastes are a little more artsy, you might get a ticket to a show by The New Provincetown Players or The Gold Dust Orphans. Alternately, you might just want to sit on the beach and contemplate the ocean.
Two last points: First off, don't try to drive down Commercial Street, at least during the summer. You'll spend hours honking at bewildered natives and hostile visitors and searching for a turnoff. Second, don't stare. One of the nicest things about Provincetown is the laid-back feeling of acceptance that it seems to generate. Although its many gay residents may not approve of my heterosexual lifestyle, they generally are kind enough to keep their opinions to themselves. I like to reciprocate.
Have a great time!